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Loneliness, Mistakes, and the Inner Questionnaire

1. You know what’s a mess? I mean, it’s a good mess to have, I guess, but when you start dating someone, and it’s okay, and then a few dates later you know it’s not great, but it’s also fine. What then? Especially if you have like three of these things going on at once. Because partially you wonder if maybe it’ll get better or more interesting as it goes along, but you also know you’re kidding yourself. Probably. But then it seems like a big hassle to break things off honestly (“no it’s actually fine, I do basically like you? I don’t know, just not that much, although maybe I would eventually. But I guess I don’t want to stick around and find out”). So everything festers.

I have no problem being straightforward with people, it’s just this middle-ground area where I’m not even sure how to be straightforward or exactly why I’m breaking things off. God, I’m not even sure what my question is. But what have you done in situations like this? Is there like an inner questionnaire you can ask yourself to decide if someone is worth keeping around? Or do we just instinctively know?

The last time I started seeing someone and wasn’t sure how I felt about her, I did what you’re probably doing right now: I thought it was just a decision I had to make, and I put it off. Surprise! It didn’t end well. Actually it ended terribly. Eventually it turned into a relationship, and eventually the way we felt about each other got more and more out of sync. By the time she was at “I love you” I was still at “I, uh, um, I—”

Right now your relationships are only a little asymmetrical. But if you’re not careful, they will continue to grow, and what seems like a hassle now will turn into a train wreck six months from now. You just don’t want to pull the trigger. And I don’t blame you, we’re trained to love choice and the idea of closing off a potential option is scary. But it’s also necessary. 

Oh, and you need to be honest with these guys, but you don’t need to be that honest. “I think you’re a great person but I just don’t have feelings for you.” That’ll sting a little, but mostly it’ll just be disappointment that something didn’t work out, it won’t be anger at you for being somehow deceiving. Eight months from now, that same sentence will sound a lot different.

You do instinctively know, you said it yourself. Don’t mistake a lack of feeling for a choice that still needs to be made. It sounds like your gut made the choice already.

2. Who’s the most surprising person you’ve been attracted to?

This is a tough question. I’m assuming you mean “The person you were most surprised to find yourself attracted to,” rather than “The person who most went out of their way to be unpredictable.” The answer to the latter would be a girl who burst into tears and vanished halfway through the date we were on. That was a surprise.

The former is more difficult, though. Because I don’t really know.

I was having dinner with a friend a few years ago and we were talking about her last few boyfriends, specifically: whether they constituted a Type. She didn’t find any patterns and then contrasted her dating variability with my dating predictability. This surprised me. I honestly didn’t think I had a type, so when she rattled off some descriptors of the last few girls I’d been involved with (and the pattern was clear as day), it came as a bit of a shock. Not that I had a type, just that I had been so oblivious to it.

The most surprising things about attraction are usually the things we don’t see ourselves, the things that our friends point out to us, or choose not to point out to us.

But, that being said: Elaine Stritch.

3. What was the best thing you did last weekend? What was the best thing you did last year? The first thing that comes to mind.

Well, it didn’t technically happen last weekend, but the weekend before that we had a bit of a blizzard (you may have heard the weather channel screaming their heads off about it). I love seasons, I love the cycles and the change and the visceral feeling of the passage of time. I grew up in Connecticut, so seasons are a part of how I understand the world to be, but I live in Manhattan now, and the last few years have been a bit of a let down, snow-wise.

Snow here is magic. People tend to get a bit saccharine when they talk about it, but that’s because there really is something special about snow falling in the city, how quiet everything gets, how everyone starts to look up, how, even though you’re in the middle of this wholly built environment, you’re reminded that you’re never really disconnected from nature.

So even though the governor told me to stay home and even though the MTA might have shut down at any time, I went out. The party I went to was fun, but the best part of the night was the walk home, a quiet city, snow falling, peaceful.

As for the best thing that happened last year, the first thing that pops to mind is the wedding I officiated. It turns out, priests and rabbis aren’t too keen on mixed-faith ceremonies, so my friends asked me to do it. I was touched and honored and jumped at the chance immediately.

It only dawned on me a little later what I had actually signed up to do. There would be a solid 20 minutes on their most special day wherein, at any moment, I could ruin everything. I could say the wrong name, sneeze on someone, pass out, or forget how to read, and endless list of ways to screw it up were running through my head. When the day finally approached, I did my best to keep it under wraps, but I was exceedingly nervous. Those little pips on a tuxedo shirt aren’t easy to put in on a good day, when you’re hands are shaking it’s almost impossible.

But the ceremony went off without a hitch. A couple good laugh lines, a cute anecdote about how they met, repeat after me. I got to stand up in front of all their friends and family and tell these two people just how much they meant to me, and how much of an inspiration they were. That was the best thing.

(And plus, during the reception, both a priest and a rabbi who were friends of the family and at the ceremony, came up to me to tell me what a good job I’d done. So, I guess I’m available for hire if anyone needs an officiant. I’ve got papers.)

4. My boyfriend and I are best friends with this other dude. The other night after my boyfriend had returned from being out of town for several weeks, we were in the back seat of this dude’s car and horny as hell, and … basically I began giving my boyfriend a sneaky blow job. It was a long drive, it was dark, the driver was preoccupied with the road, and our friend seemed to be drifting off to sleep in the passenger’s seat … until he turned back at one point and saw us. We didn’t think we’d get caught, and we definitely didn’t think of the consequences. This best dude friend was clearly upset, and has since talked to us individually, conversations during which we both apologized endlessly, and he claims to be “not mad anymore.” He’s understandably still upset, though (I feel like with me more so than my boyfriend?), and while I wish I could take it back, I can’t. This friend is not a prude, we’re all pretty open about sex, and my boyfriend and I feel like we’ll eventually all laugh about it, but I really feel so terrible for making him uncomfortable in his own vehicle and being so inconsiderate to him. How can I ease the process of us getting over this as quickly as possible? Basically my question or the advice I’m looking for is how can I make this better? Buy him gifts? Take him out to dinner? Offer him our first born child?

Yeesh. Well, yes, you definitely need to make it up to him, but gifts and dinner aren’t going to do it. Those things will just draw attention to the fact that this violation happened, they’ll be a constant reminder of the event. He’s probably torn by his desire to forget it ever happened and his desire to remind you that you did something wrong.

Try this: just be a little nicer to him. Don’t go out of your way to keep addressing what happened, don’t address it at all, just defer to him a little bit more. See the movie he wants to see, go to the restaurant he wants to go to, but don’t make it seem like you’re doing it on purpose, don’t pick up the check or buy him a popcorn, he’s not a toddler. You just want to remind him, with the little things, that he’s important to you.

And definitely don’t do it again.

5. How common is it for the average guy to visit a prostitute? I was shocked when my boyfriend told me that he had, on more than one occasion, paid for sex. I suppose I always just had a vague idea that men who consorted with hookers were creepy, or desperate, or misogynists. But my boyfriend is none of those things, and now I don’t know what to think. I had no idea what to make of this information, because I don’t know what kind of person visits prostitutes — or if there is one — because I don’t know any. Or, I don’t know anybody who will say that they do. He claims that he has heard some stories from other men, and that it’s probably something that guys don’t normally talk about with their girlfriends or female friends. He did say he wasn’t surprised that I was shocked. Shocked is, I think, an understatement. A bit of backstory here: it happened years ago, and for a variety of reasons, but mostly boiling down to loneliness. I’m not worried about him cheating on me or anything, and he says he wouldn’t do it again today. He’s a great guy who treats me well, but as I said, I have no point of reference as to what this may or may not indicate about him. So, is it normal for prostitutes to be weaved into somebody’s sexual history, or should I take this as a red flag?

I’ve never visited a prostitute. I don’t think any of my friends have, but we’ve never talked about it. I don’t know even much about prostitutes, aside from movies and TV.

But I do known a lot about loneliness. From your description of the back story, it doesn’t sound like this was a raucous bachelor party or some wild, coke-fueled trip to Vegas. That would be a red flag. It sounds like he was lonely and wanted to feel some companionship, even temporarily. That desire is normal. That desire is universal. He might have tried to address it in a way you find off-putting, but in the end, that’s all he was really trying to do.

To be honest, I didn’t expect myself to answer this way. I’ve never really been faced with this question, and my long-running assumptions about the people who “consort” with prostitutes weren’t much different than yours. But if I really think about it, and think about a person who just wants someone else, for a little while, to acknowledge his existence, it’s doesn’t seem creepy, it seems sad. And it is sad. But that’s okay.

Look, if anything, the prostitutes aren’t a red flag, but you may want to recognize that your boyfriend has the propensity for a deep, desperate loneliness. But, unless I’m mistaken, he’s human, so that’s to be expected.


Previously: Boyfriends’ Mothers, “Compassion,” and Les Misérables

A Dude is one of several rotating dudes. Do you have a question for A Dude?


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